Isobutanol → HCID 70457302, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the triphenyl phosphite-chlorine kinetic complex was prepared by adding chlorine gas simultaneously with 3.16 ml (12 mmol) of triphenyl phosphite to 45 ml of methylene chloride at -10° C. A slight yellow color was maintained throughout the preparation. An additional 0.5 mmol of triphenyl phosphite was added to dissipate the yellow chlorine color. To the resulting solution was added 4.84 gm (10 mmol) of 4'-nitrobenzyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate which was washed into the mixture with 5 ml of methylene chloride. After 5 minutes 1.8 ml (13 mmol) of triethylamine in 8 ml of methylene chloride were added over a 15 minute period. After stirring the reaction mixture for 15 minutes at -10° C., the cooling bath was removed from the reaction mixture and 5.1 ml (55 mmol) of isobutanol was added. Thereafter HCl gas was bubbled into the reaction mixture for about 3 minutes. The reaction mixture was seeded and allowed to warm to room temperature. After 2 hours at room temperature the reaction mixture was filtered to provide 1.28 grams (33.2%) of the nucleus hydrochloride ester: m.p. 180.5° C. (dec.).

Provenance & Evidence